US20090105102A1 - Benzotriazole Compositions - Google Patents

Benzotriazole Compositions Download PDF

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Publication number
US20090105102A1
US20090105102A1 US11/667,779 US66777905A US2009105102A1 US 20090105102 A1 US20090105102 A1 US 20090105102A1 US 66777905 A US66777905 A US 66777905A US 2009105102 A1 US2009105102 A1 US 2009105102A1
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Prior art keywords
alkyl
cycloalkyl
phenyl
represents hydrogen
group
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US11/667,779
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English (en)
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Isabelle Rapenne-Jacob
Samuel Evans
Peter Rohrbach
Martin Von Buren
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BASF Corp
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Individual
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Assigned to CIBA SPECIALTY CHEMICALS CORP. reassignment CIBA SPECIALTY CHEMICALS CORP. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ROHRBACH, PETER, EVANS, SAMUEL, VON BUEREN, MARTIN, RAPENNE-JACOB, ISABELLE
Publication of US20090105102A1 publication Critical patent/US20090105102A1/en
Priority to US13/019,567 priority Critical patent/US20110212864A1/en
Abandoned legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M141/00—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential
    • C10M141/06—Lubricating compositions characterised by the additive being a mixture of two or more compounds covered by more than one of the main groups C10M125/00 - C10M139/00, each of these compounds being essential at least one of them being an organic nitrogen-containing compound
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
    • C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
    • C10M133/38—Heterocyclic nitrogen compounds
    • C10M133/44—Five-membered ring containing nitrogen and carbon only
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C10M2203/10—Petroleum or coal fractions, e.g. tars, solvents, bitumen
    • C10M2203/1006—Petroleum or coal fractions, e.g. tars, solvents, bitumen used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/02—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers
    • C10M2205/028—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms
    • C10M2205/0285—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions containing acyclic monomers containing aliphatic monomers having more than four carbon atoms used as base material
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/026—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with tertiary alkyl groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/287—Partial esters
    • C10M2207/289—Partial esters containing free hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/064—Di- and triaryl amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2020/00—Specified physical or chemical properties or characteristics, i.e. function, of component of lubricating compositions
    • C10N2020/01—Physico-chemical properties
    • C10N2020/02—Viscosity; Viscosity index
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/10—Inhibition of oxidation, e.g. anti-oxidants
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/14—Metal deactivation
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/08—Hydraulic fluids, e.g. brake-fluids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2040/00—Specified use or application for which the lubricating composition is intended
    • C10N2040/20—Metal working
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2050/00—Form in which the lubricant is applied to the material being lubricated
    • C10N2050/023—Multi-layer lubricant coatings

Definitions

  • the invention relates to novel benzotriazole compositions comprising mixtures of benzotriazoles and N-substituted benzotriazoles, the process for preparing N-substituted benzotriazoles and a method for improving the functional properties of lubricants, hydraulic or metal-working fluids or coating compositions.
  • Additives which can be used as metal deactivators display their protective action in functional liquids, such as mineral oil or fuels, by deactivating the metal ions, such as copper or iron, contained therein. These metal ions can have catalytic effects in undesired oxidative decomposition processes of mineral oil or fuels.
  • the protective action is explained by the formation of film-like layers on the surface of metals or by complex formation with metal ions.
  • EP-A-365 476 discloses benzotriazole compounds:
  • R 1 represents C 1 -C 12 straight or branched chain alkyl
  • R 2 represents C 1 -C 12 straight or branched chain alkyl interrupted by one or more O-atoms or represents C 5 -C 12 cycloalkyl;
  • metal deactivators of the triazole type are problematic. Because of high temperatures, in particular in internal combustion engines and turbines, which are exposed to oils and fuels, the deactivator concentration can rapidly decrease with a corresponding reduction in the protective action.
  • TTA tolutriazole
  • alkyl aldehydes and cycloalkanols additive components which can be used in lubricant compositions as metal deactivators, possess improved solubility and, in functional liquids, have lower volatility than tolutriazole itself.
  • the invention relates to a composition
  • a composition comprising
  • compositions defined above are prepared by conventional mixing procedures and are suitable as metal deactivators in functional liquids.
  • compositions according to the invention are defined by the following isomeric structures:
  • R 1 , R 2 and R 3 are as defined above.
  • isomer includes any structural and positional isomers, tautomeric forms, cis-trans isomers and stereoisomers, e.g. enantiomeric forms and racemic mixtures.
  • R 1 and R 1 ′ defined as C 1 -C 4 alkyl represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl. According to a preferred embodiment, R 1 represents methyl.
  • R 2 represents a substituent selected from the group consisting of C 1 -C 12 alkyl, C 5 -C 7 cycloalkyl, (C 1 -C 4 alkyl) 1-3 C 5 -C 7 cycloalkyl or C 5 -C 7 cycloalkyl-C 1 -C 4 alkyl.
  • R 2 defined as C 1 -C 12 alkyl represents C 1 -C 4 alkyl as defined above with regard to R 1 and R 1 ′ and additionally represents straight chain or branched C 5 -C 12 alkyl, e.g. pentyl, hexyl, heptyl, octyl, nonyl, undecyl or dodecyl.
  • R 2 defined as C 5 -C 7 cycloalkyl is preferably cyclopentyl or cyclohexyl.
  • C 5 -C 7 cycloalkyl is preferably cyclopentyl or cyclohexyl substituted with C 1 -C 4 alkyl, e.g. methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl.
  • R 2 defined as C 5 -C 7 cycloalkyl-C 1 -C 4 alkyl is e.g. cyclopentylmethyl, cyclohexylmethyl, cyclopentyl-1,1-ethyl, cyclohexyl-1,1-ethyl, cyclopentyl-1,2-ethyl or cyclohexyl-1,2-ethyl.
  • the index a represents a numeral from 1 to 10
  • the index n represents a numeral from 2 to 8.
  • the index a represents a numeral from 1 to 6
  • the index n represents a numeral from 2 to 6.
  • the index a represents a numeral from 1 to 4
  • the index n represents a numeral from 2 to 4.
  • R 3 represents a substituent a substituent selected from the group consisting of C 1 -C 12 alkyl, C 5 -C 7 cycloalkyl, (C 1 -C 4 alkyl) 1-3 C 5 -C 7 cycloalkyl, C 5 -C 7 cycloalkyl-C 1 -C 4 alkyl, phenyl, phenyl-C 1 -C 4 alkyl, (C 1 -C 4 alkyl) 1-3 phenyl and (C 1 -C 4 alkyl) 1-3 phenyl-C 1 -C 4 alkyl.
  • R 3 defined as C 1 -C 12 alkyl, C 5 -C 7 cycloalkyl, (C 1 -C 4 alkyl) 1-3 C 5 -C 7 cycloalkyl and C 5 -C 7 cycloalkyl-C 1 -C 4 alkyl has the same meanings as defined above with regard to R 2 .
  • R 3 defined as phenyl, phenyl-C 1 -C 4 alkyl, (C 1 -C 4 alkyl) 1-3 phenyl and (C 1 -C 4 alkyl) 1-3 phenyl-C 1 -C 4 alkyl is, for example, phenyl, benzyl, 1- or 2-phenylethyl, 4-methyl or 4-ethyl, cumyl or 4-methylbenzyl.
  • Suitable acid catalysts include mineral acids, e.g. sulphuric acid, acid clays, e.g. bentonite, montmorillonite, Bleicherde Tonsil® (Supreme 110 FF, 126 FF) or Fuller's earth, acid ion-exchange resins, e.g. Amberlyst® 15, and sulphonic acids, e.g. p-toluene sulphonic acid.
  • mineral acids e.g. sulphuric acid
  • acid clays e.g. bentonite, montmorillonite, Bleicherde Tonsil® (Supreme 110 FF, 126 FF) or Fuller's earth
  • acid ion-exchange resins e.g. Amberlyst® 15
  • sulphonic acids e.g. p-toluene sulphonic acid.
  • the inert solvent may be cyclohexane, benzene, toluene, xylene or carbon tetrachloride.
  • R 1 defined as C 1 -C 4 alkyl represents methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl. According to a preferred embodiment, R 1 represents methyl.
  • Compounds (II) are known and are commercially available, e.g. Irgamet® (Ciba Specialty Chemicals) TTA.
  • compositions according to the invention are preferably defined by the following isomeric structure:
  • R 1 , R 2 and R 3 are as defined above.
  • Compounds (III), according to the optional component c), can be prepared in a manner analogous to EP 0 365 476, e.g. by the acid catalysed reaction of a R 1 -substituted triazole, e.g. triazole or methyltriazole, with the aldehyde R 3 —C( ⁇ O)—H and the alcohol R 2 —OH.
  • a R 1 -substituted triazole e.g. triazole or methyltriazole
  • Compounds (III), wherein R 2 represents a group of the partial formula (A) or (B), can be pre-pared in an analogous manner by the acid catalysed reaction of the R 1 -substituted triazole, e.g. triazole or methyltriazole, with the diol HO—(CH 2 ) 2-3 O—(CH 2-3 O) a —(CH 2-3 )—OH and 2 equivalents of the aldehyde R 3 —(C ⁇ O)—H, or with the diol HO—(CH 2 ) n —OH and 2 equivalents of the aldehyde R 3 —(C ⁇ O)—H.
  • the R 1 -substituted triazole e.g. triazole or methyltriazole
  • the term functional liquid selected from the group consisting of lubricants, hydraulic agents, metal working fluids and coating agents includes non-aqueous, partially aqueous and aqueous liquids which are in contact with metals to be deactivated, in particular copper or iron.
  • non-aqueous functional liquids are fuels, e.g. hydrocarbon mixtures comprising mineral oil fractions which are liquid at room temperature and are suitable for use in internal combustion engines, e.g. internal combustion engines with external (petrol engines) or internal ignition (diesel engines), e.g. petrol having different octane contents (regular grade or premium grade petrol) or diesel fuel, and lubricants, hydraulic fluid, metal working fluid, engine coolants, transformer oil and switch gear oil.
  • fuels e.g. hydrocarbon mixtures comprising mineral oil fractions which are liquid at room temperature and are suitable for use in internal combustion engines, e.g. internal combustion engines with external (petrol engines) or internal ignition (diesel engines), e.g. petrol having different octane contents (regular grade or premium grade petrol) or diesel fuel, and lubricants, hydraulic fluid, metal working fluid, engine coolants, transformer oil and switch gear oil.
  • Suitable partially aqueous functional liquids are hydraulic fluids based on aqueous polyglycol/polyglycol ether mixtures or glycol systems, water-in-oil or oil-in-water systems and engine cooling systems based on aqueous glycol.
  • aqueous functional liquids are industrial cooling water, filling compositions of a water conditioning plant, steam generation systems, sea water evaporation systems, sugar evaporation systems, irrigation systems, hydrostatic boilers and heating systems or cooling systems having a closed circulation.
  • compositions according to the invention preferably comprise 0.01 to 5.0% by weight, in particular 0.02 to 1.0% by weight, of a compound (I), based on the weight of the functional liquid.
  • Non-aqueous functional liquids are preferred, in particular base oils of lubricating viscosity, which can be used for the preparation of greases, metal working fluids, gear fluids and hydraulic fluids.
  • Suitable greases, metal working fluids, gear fluids and hydraulic fluids are based, for example, on mineral or synthetic oils or mixtures thereof.
  • the lubricants are familiar to a person skilled in the art and are described in the relevant literature, such as, for example, in Chemistry and Technology of Lubricants ; Mortier, R. M. and Orszulik, S. T. (Editors); 1992 Blackie and Son Ltd. for GB, VCH-Publishers N.Y. for U.S., ISBN 0-216-92921-0, cf. pages 208 et seq. and 269 et seq.; in Kirk - Othmer Encyclopedia of Chemical Technology, Fourth Edition 1969, J. Wiley & Sons, New York, Vol.
  • the lubricants are in particular oils and greases, for example based on mineral oil or vegetable and animal oils, fats, tallow and wax or mixtures thereof.
  • Vegetable and animal oils, fats, tallow and wax are, for example, palm kernel oil, palm oil, olive oil, colza oil, rapeseed oil, linseed oil, soy bean oil, cotton wool oil, sunflower oil, coconut oil, maize oil, castor oil, walnut oil and mixtures thereof, fish oils, and chemically modified, e.g. epoxidised or sulphoxidised, forms or forms prepared by genetic engineering, for example soy bean oil prepared by genetic engineering.
  • Examples of synthetic lubricants include lubricants based on aliphatic or aromatic carboxylic esters, polymeric esters, polyalkylene oxides, phosphoric acid esters, poly- ⁇ -olefins or silicones of the diester of a dibasic acid with a monohydric alcohol, e.g. dioctyl sebacate or dinonyl adipate, of a triester of trimethylolpropane with a monobasic acid or with a mixture of such acids, e.g.
  • trimethylolpropane tripelargonate trimethylolpropane tricaprylate or mixtures thereof, of a tetra ester of pentaerythritol with a monobasic acid or with a mixture of such acids, e.g. pentaerythrityl tetracaprylate, or of a complex ester of monobasic and dibasic acids with polyhydric alcohols, e.g. a complex ester of trimethylolpropane with caprylic and sebacic acid or of a mixture thereof.
  • Particularly suitable in addition to mineral oils are, for example, poly- ⁇ -olefins, ester-based lubricants, phosphates, glycols, polyglycols and polyalkylene glycols and mixtures thereof with water.
  • Said lubricants or mixtures thereof can also be mixed with an organic or inorganic thickener (base fat).
  • Organic or inorganic thickener base fat
  • Metal working fluids and hydraulic fluids can be prepared on the basis of the same substances as described above for the lubricants. These are frequently also emulsions of such substances in water or other liquids.
  • a further embodiment of the invention relates to a composition, which comprises additional additives selected from the group consisting of metal deactivators, antioxidants, rust inhibitors, viscosity index improvers, pour-point depressants, dispersants, surfactants, extreme-pressure additives, and antiwear additives.
  • additional additives selected from the group consisting of metal deactivators, antioxidants, rust inhibitors, viscosity index improvers, pour-point depressants, dispersants, surfactants, extreme-pressure additives, and antiwear additives.
  • additives are added in the amounts customary in each case for the purpose, each in the range from 0.01 to 10.0% by weight. Examples of further additives are listed below:
  • Said components can be mixed with the lubricants in a manner known per se. It is also possible to prepare a concentrate or a so-called additive packet, which can be diluted to the concentrations of use for the corresponding lubricant according to consumption.
  • the invention particularly refers to a composition comprising
  • the mixtures defined above is particularly useful in method for improving the functional properties of lubricants, hydraulic or metal-working fluids or coating compositions, which comprises adding to a functional fluid the mixture defined above and, optionally, further additives.
  • Montmorillonit is replaced with Bleicherde Tonsil® Supreme 110FF.
  • a 0.05% solution of the test composition in a mineral oil of turbine quality is prepared, which oil has a viscosity of 26.2 mm 2 /sec (40° C.) and 4.8 mm 2 /sec (100° C.) and a sulphur content of 0.54%.
  • the solution can also contain a phenolic or amine antioxidant. The time required at a temperature of 150° C. for a minimum pressure drop of 1.75 bar starting from the maximum pressure of 6.2 bar is measured.
  • a copper strip (50 ⁇ 10 ⁇ 1 mm) is polished with grade 150 silicon carbide, which was absorbed with a wool pad wet with high-boiling petroleum ether. The polished strip is then completely immersed in the prepared solution, which is kept at 100° C. for two hours. The strip is then removed, washed with isooctane and dried and its colour is compared with the standardized colour samples of the tarnish chart, which is applicable for the corrosion test of copper strips according to ASTM D130.
  • Control 1 Control 2 Control 3 1 (B-1) 2 (B-2) 3 (B-3) 4 (B-4) 5 (B-5) 6 (B-6) 7 (B-7) Base Fluid 1)
  • B-1) Control 2
  • B-2) Control 3 1 (B-1) 2 (B-2) 3 (B-3) 4 (B-4) 5 (B-5) 6 (B-6) 7 (B-7)
  • Base Fluid 1 Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal. Bal.
  • Test Control 1 Control 2 Control 3 1 (B-1) 2 (B-2) 3 (B-3) 4 (B-4) 5 (B-5) 6 (B-6) 7 (B-7) RPVOT 1) 28 452 507 581 582 646 640 640 645 651 D 130 rating 4a 4a 3b 1b+ 1b+ 1b+ 1b+ 1b+ 1b+ 1) RPVOT: Average of duplicates, minutes; ASTM D 2272 2) Copper corrosion per ASTM D 130, 3 h at 125° C. with 50 ppm elemental sulphur present

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Chemistry (AREA)
  • Lubricants (AREA)
  • Preventing Corrosion Or Incrustation Of Metals (AREA)
US11/667,779 2004-11-22 2005-11-14 Benzotriazole Compositions Abandoned US20090105102A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US13/019,567 US20110212864A1 (en) 2004-11-22 2011-02-02 Benzotriazole compositions

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP04105973 2004-11-22
EP04105973.4 2004-11-22
PCT/EP2005/055934 WO2006053858A1 (en) 2004-11-22 2005-11-14 Benzotriazole compositions

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EP (1) EP1833953A1 (enrdf_load_stackoverflow)
JP (1) JP2008520784A (enrdf_load_stackoverflow)
CN (1) CN101061206A (enrdf_load_stackoverflow)
BR (1) BRPI0518001A (enrdf_load_stackoverflow)
CA (1) CA2586083A1 (enrdf_load_stackoverflow)
TW (1) TW200621731A (enrdf_load_stackoverflow)
WO (1) WO2006053858A1 (enrdf_load_stackoverflow)

Cited By (3)

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US20110212864A1 (en) * 2004-11-22 2011-09-01 Isabelle Rapenne-Jacob Benzotriazole compositions
US11788026B2 (en) 2021-07-28 2023-10-17 Afton Chemical Corporation Hydraulic fluid
US12018224B2 (en) 2021-07-28 2024-06-25 Afton Chemical Corporation Hydraulic fluid

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US8236205B1 (en) 2011-03-11 2012-08-07 Wincom, Inc. Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles and other triazoles and methods for using same
US8236204B1 (en) 2011-03-11 2012-08-07 Wincom, Inc. Corrosion inhibitor compositions comprising tetrahydrobenzotriazoles solubilized in activating solvents and methods for using same
CN103450102B (zh) * 2013-05-08 2016-03-09 如皋市金陵化工有限公司 1－正丁基－1h－苯并三氮唑的合成工艺
SG11201600138XA (en) * 2013-07-11 2016-02-26 Basf Se Chemical-mechanical polishing composition comprising benzotriazole derivatives as corrosion inhibitors
US9309205B2 (en) 2013-10-28 2016-04-12 Wincom, Inc. Filtration process for purifying liquid azole heteroaromatic compound-containing mixtures
CN104649985A (zh) * 2013-11-25 2015-05-27 刘现梅 一种水溶性的甲基苯骈三氮唑的次甲基衍生物及其制备方法
CN107987917A (zh) * 2017-12-11 2018-05-04 国网福建省电力有限公司 一种变压器油中硫腐蚀防护方法

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US11788026B2 (en) 2021-07-28 2023-10-17 Afton Chemical Corporation Hydraulic fluid
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CA2586083A1 (en) 2006-05-26
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EP1833953A1 (en) 2007-09-19
TW200621731A (en) 2006-07-01
BRPI0518001A (pt) 2008-10-21
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